Formation of 1,4-diketones by aerobic oxidative C-C coupling of styrene with 1,3-dicarbonyl compounds

被引:58
|
作者
Rössle, M [1 ]
Werner, T [1 ]
Baro, A [1 ]
Frey, W [1 ]
Christoffers, J [1 ]
机构
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
关键词
dicarbonyl compounds; C-C coupling; cerium; heterocycles; homogeneous catalysis;
D O I
10.1002/anie.200461406
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical equation presented). Convenient and direct: 1,4-Dicarbonyl compounds are readily obtained through a one-pot cerium-catalyzed oxidative C-C coupling in the presence of oxygen and subsequent fragmentation. The products are suitable precursors for heterocycles.
引用
收藏
页码:6547 / 6549
页数:3
相关论文
共 50 条
  • [1] Lanthanide-Catalyzed Oxidative C-O Coupling of 1,3-Dicarbonyl Compounds with Diacyl Peroxides
    Terent'ev, Alexander O.
    Vil', Vera A.
    Nikishin, Gennady I.
    Adam, Waldemar
    SYNLETT, 2015, 26 (06) : 802 - 806
  • [2] HY and Hβ Zeolites Mediated C-C Bond Formation via Addition/Substitution Reaction of 1,3-Dicarbonyl Compounds to Alcohols and Alkenes
    Boosa, Murali
    Yennamaneni, Divya Rohini
    Chevella, Durgaiah
    Amrutham, Vasu
    Gajula, Krishna Sai
    Madasu, Ramulamma
    Akula, Venugopal
    Nama, Narender
    CATALYSIS LETTERS, 2023, 153 (05) : 1349 - 1358
  • [3] Copper(II)-Promoted C-C Bond Formation by Oxidative Coupling of Two C(sp3)-H Bonds Adjacent to Carbonyl Group to Construct 1,4-Diketones and Tetrasubstituted Furans
    Mao, Shuai
    Gao, Ya-Ru
    Zhang, Shao-Liang
    Guo, Dong-Dong
    Wang, Yong-Qiang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (04) : 876 - 885
  • [4] CAN-based oxidative annulation of alkenols with 1,3-dicarbonyl compounds
    Dariusz Cież
    Krzysztof Kozieł
    Branislav Horváth
    Jan Světlík
    Monatshefte für Chemie - Chemical Monthly, 2018, 149 : 1849 - 1855
  • [5] CAN-based oxidative annulation of alkenols with 1,3-dicarbonyl compounds
    Ciez, Dariusz
    Koziel, Krzysztof
    Horvath, Branislav
    Svetlik, Jan
    MONATSHEFTE FUR CHEMIE, 2018, 149 (10): : 1849 - 1855
  • [6] Cyclization of o-Alkynylisocyanobenzenes with 1,3-Dicarbonyl Compounds
    La-ongthong, Kannika
    Sawekteeratana, Natthapat
    Klaysuk, Jasarin
    Soorukram, Darunee
    Leowanawat, Pawaret
    Reutrakul, Vichai
    Krobthong, Sucheewin
    Wongtrakoongate, Patompon
    Kuhakarn, Chutima
    SYNLETT, 2022, 33 (14) : 1411 - 1418
  • [7] Cerium-catalyzed, aerobic oxidative synthesis of 1,2-dioxane derivatives from styrene and their fragmentation into 1,4-dicarbonyl compounds
    Rössle, M
    Werner, T
    Frey, W
    Christoffers, J
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (23) : 5031 - 5038
  • [8] Copper(II) Triflate Catalyzed Amination of 1,3-Dicarbonyl Compounds
    Thi My Uyen Ton
    Himawan, Fanny
    Chang, Joyce Wei Wei
    Chan, Philip Wai Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (38) : 12020 - 12027
  • [9] TiIV-catalyzed asymmetric sulfenylation of 1,3-dicarbonyl compounds
    Jereb, Marian
    Togni, Antonio
    CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (33) : 9384 - 9392
  • [10] Potassium Persulfate Mediated Oxidative Radical Cyclization of 1,3-Dicarbonyl Compounds with Styrenes for the Synthesis of Dihydrofurans
    Wang, Shun
    He, Lin-Ye
    Guo, Li-Na
    SYNTHESIS-STUTTGART, 2015, 47 (20): : 3191 - 3197